JP2020502213A5 - - Google Patents
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- JP2020502213A5 JP2020502213A5 JP2019533489A JP2019533489A JP2020502213A5 JP 2020502213 A5 JP2020502213 A5 JP 2020502213A5 JP 2019533489 A JP2019533489 A JP 2019533489A JP 2019533489 A JP2019533489 A JP 2019533489A JP 2020502213 A5 JP2020502213 A5 JP 2020502213A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- alkyl
- phenyl
- cyclopropyl
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 50
- 125000001424 substituent group Chemical group 0.000 claims 45
- -1 pyrazole-4-yl Chemical group 0.000 claims 40
- 208000002193 Pain Diseases 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 201000010099 disease Diseases 0.000 claims 19
- 229910052731 fluorine Inorganic materials 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- 208000011580 syndromic disease Diseases 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 239000005711 Benzoic acid Substances 0.000 claims 9
- 235000010233 benzoic acid Nutrition 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 208000024891 symptom Diseases 0.000 claims 9
- 206010035664 Pneumonia Diseases 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 5
- 201000009273 Endometriosis Diseases 0.000 claims 5
- 206010030113 Oedema Diseases 0.000 claims 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 201000008482 osteoarthritis Diseases 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- 230000001154 acute effect Effects 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 4
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 201000005569 Gout Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 206010020853 Hypertonic bladder Diseases 0.000 claims 3
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 3
- 206010033645 Pancreatitis Diseases 0.000 claims 3
- 206010033799 Paralysis Diseases 0.000 claims 3
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims 3
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 208000020629 overactive bladder Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 230000002792 vascular Effects 0.000 claims 3
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 206010003645 Atopy Diseases 0.000 claims 2
- 229920000742 Cotton Polymers 0.000 claims 2
- 206010011796 Cystitis interstitial Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 206010061979 Genital pain Diseases 0.000 claims 2
- 206010019233 Headaches Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 241000208125 Nicotiana Species 0.000 claims 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 2
- 208000000450 Pelvic Pain Diseases 0.000 claims 2
- 208000003251 Pruritus Diseases 0.000 claims 2
- 201000010001 Silicosis Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010042496 Sunburn Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- 239000003610 charcoal Substances 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 206010013990 dysuria Diseases 0.000 claims 2
- 231100000869 headache Toxicity 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 230000002175 menstrual effect Effects 0.000 claims 2
- 230000004060 metabolic process Effects 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 206010034674 peritonitis Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 201000008827 tuberculosis Diseases 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- SPLLGXCKZJCOGA-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound S1C(=CC2=C1C=CC=C2)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F SPLLGXCKZJCOGA-UHFFFAOYSA-N 0.000 claims 1
- ZWELQKMKGRLXGD-UHFFFAOYSA-N 2-(1-cyclobutyl-3-fluoropyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=C(C(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F)F ZWELQKMKGRLXGD-UHFFFAOYSA-N 0.000 claims 1
- SLZUUKYITSTWIN-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-(2-fluoro-4-methylphenyl)cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)C)F SLZUUKYITSTWIN-UHFFFAOYSA-N 0.000 claims 1
- IUUOOSSNXCCWSG-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-(5-fluoropyridin-2-yl)cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=NC=C(C=C1)F IUUOOSSNXCCWSG-UHFFFAOYSA-N 0.000 claims 1
- LHYDLFVHSXREDW-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)OC(F)(F)F)F LHYDLFVHSXREDW-UHFFFAOYSA-N 0.000 claims 1
- WGJDSFNBLJOHPM-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F WGJDSFNBLJOHPM-UHFFFAOYSA-N 0.000 claims 1
- XJDQTSXXOYYQPM-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=CC(=C(C=C1)C(F)(F)F)F XJDQTSXXOYYQPM-UHFFFAOYSA-N 0.000 claims 1
- FMLUTSJYVCQXGM-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-[4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=CC=C(C=C1)OC(F)(F)F FMLUTSJYVCQXGM-UHFFFAOYSA-N 0.000 claims 1
- INGVSMJXHRAHKR-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-3-fluoro-5-[[1-[4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=CC=C(C=C1)C(F)(F)F INGVSMJXHRAHKR-UHFFFAOYSA-N 0.000 claims 1
- OTKADLJLSKIEFF-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-5-[[1-(2,4-difluorophenyl)cyclopropanecarbonyl]amino]-3-fluorobenzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)F)F OTKADLJLSKIEFF-UHFFFAOYSA-N 0.000 claims 1
- CDTASRIWCPXZDF-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-5-[[1-(3,4-difluorophenyl)cyclopropanecarbonyl]amino]-3-fluorobenzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=CC(=C(C=C1)F)F CDTASRIWCPXZDF-UHFFFAOYSA-N 0.000 claims 1
- SMHPXSBGGKDSSM-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]-3-methylbenzoic acid Chemical compound Cc1cc(NC(=O)C2(CC2)c2ccc(OC(F)(F)F)cc2F)cc(C(O)=O)c1-c1cnn(c1)C1CCC1 SMHPXSBGGKDSSM-UHFFFAOYSA-N 0.000 claims 1
- XKTGTXHJMCTLNP-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)OC(F)(F)F)F XKTGTXHJMCTLNP-UHFFFAOYSA-N 0.000 claims 1
- AJWVHJYOBHSPFW-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]-3-methylbenzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1C)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F AJWVHJYOBHSPFW-UHFFFAOYSA-N 0.000 claims 1
- DFQFSWDEFZCQLH-UHFFFAOYSA-N 2-(1-cyclobutylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F DFQFSWDEFZCQLH-UHFFFAOYSA-N 0.000 claims 1
- BTXJPCQSTIYZTA-UHFFFAOYSA-N 2-(1-cyclohexylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCCCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)OC(F)(F)F)F BTXJPCQSTIYZTA-UHFFFAOYSA-N 0.000 claims 1
- QLXDHHAUENNNDY-UHFFFAOYSA-N 2-(1-cyclohexylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCCCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F QLXDHHAUENNNDY-UHFFFAOYSA-N 0.000 claims 1
- XDYVLUWLMVALAZ-UHFFFAOYSA-N 2-(1-cyclopentylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCCC1)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F XDYVLUWLMVALAZ-UHFFFAOYSA-N 0.000 claims 1
- KIZISVSWHICRJX-UHFFFAOYSA-N 2-(1-ethylpyrazol-4-yl)-3-fluoro-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C(C)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)OC(F)(F)F)F KIZISVSWHICRJX-UHFFFAOYSA-N 0.000 claims 1
- GGVADENEQQARBQ-UHFFFAOYSA-N 2-(1-ethylpyrazol-4-yl)-3-fluoro-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C(C)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F GGVADENEQQARBQ-UHFFFAOYSA-N 0.000 claims 1
- OCLFSJBHPXRQSO-UHFFFAOYSA-N 2-(1-ethylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound CCn1cc(cn1)-c1ccc(NC(=O)C2(CC2)c2ccc(OC(F)(F)F)cc2F)cc1C(O)=O OCLFSJBHPXRQSO-UHFFFAOYSA-N 0.000 claims 1
- QXCCTXLJOKMTSM-UHFFFAOYSA-N 2-(1-ethylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C(C)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F QXCCTXLJOKMTSM-UHFFFAOYSA-N 0.000 claims 1
- VIXHTTPNSKOSBV-UHFFFAOYSA-N 2-(1-tert-butylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C(C)(C)(C)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)OC(F)(F)F)F VIXHTTPNSKOSBV-UHFFFAOYSA-N 0.000 claims 1
- YUHZGIZLRDBNGP-UHFFFAOYSA-N 2-(1-tert-butylpyrazol-4-yl)-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C(C)(C)(C)N1N=CC(=C1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F YUHZGIZLRDBNGP-UHFFFAOYSA-N 0.000 claims 1
- OBMPTFTWQVGVHK-UHFFFAOYSA-N 2-(2-cyclobutyl-1,3-thiazol-5-yl)-3-fluoro-5-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)C=1SC(=CN=1)C1=C(C(=O)O)C=C(C=C1F)NC(=O)C1(CC1)C1=C(C=C(C=C1)C(F)(F)F)F OBMPTFTWQVGVHK-UHFFFAOYSA-N 0.000 claims 1
- UFCFKJIKEUMGFX-UHFFFAOYSA-N 2-(2-cyclobutyl-1,3-thiazol-5-yl)-5-[[1-(2-fluoro-4-methylphenyl)cyclopropanecarbonyl]amino]benzoic acid Chemical compound C1(CCC1)C=1SC(=CN=1)C1=C(C(=O)O)C=C(C=C1)NC(=O)C1(CC1)C1=C(C=C(C=C1)C)F UFCFKJIKEUMGFX-UHFFFAOYSA-N 0.000 claims 1
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